99948-47-7Relevant articles and documents
Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids
Jiang, Xingguo,Zhang, Jiasheng,Ma, Shengming
supporting information, p. 8344 - 8347 (2016/07/26)
Oxidation from alcohols to carboxylic acids, a class of essential chemicals in daily life, academic laboratories, and industry, is a fundamental reaction, usually using at least a stoichiometric amount of an expensive and toxic oxidant. Here, an efficient and practical sustainable oxidation technology of alcohols to carboxylic acids using pure O2 or even O2 in air as the oxidant has been developed: utilizing a catalytic amount each of Fe(NO3)3·9H2O/TEMPO/MCl, a series of carboxylic acids were obtained from alcohols (also aldehydes) in high yields at room temperature. A 55 g-scale reaction was demonstrated using air. As a synthetic application, the first total synthesis of a naturally occurring allene, i.e., phlomic acid, was accomplished.
Studies on intramolecular alkylation of an α-sulfinyl vinylic carbanion: A novel route to chiral 1-cycloalkenyl sulfoxides
Maezaki, Naoyoshi,Izumi, Mayuko,Yuyama, Sachiko,Sawamoto, Hiroaki,Iwata, Chuzo,Tanaka, Tetsuaki
, p. 7927 - 7945 (2007/10/03)
Intramolecular alkylation of various β-(ω-haloalkyl) substituted vinylic sulfoxides was investigated. Upon treatment with LDA in THF at -78°C, α-sulfinyl carbanion generated from vinylic sulfoxides cyclized at the α-sulfinyl position to give 1-cycloalkenyl sulfoxides with a five- to seven-membered ring. Although iodide or bromide is normally a good leaving group, chloride affords better results than the corresponding iodide and bromide when the reaction takes place at the benzylic position. The cyclization proceeded even with the secondary iodide in moderate yield. Not only the (E)-isomer but also the (Z)-isomer cyclized via rapid inversion of the olefin geometry. No loss of optical purity was observed during isomerization. Various 1-cycloalkenyl sulfoxides including a fused ring and a polyoxygenated rings were synthesized in good to moderate yields. (C) 2000 Elsevier Science Ltd.
